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WO1990003362A1 - 2-(alkoxyalkylaminomethyl)-4-aminophenols et leur utilisation dans des teintures oxydantes pour cheveux - Google Patents

2-(alkoxyalkylaminomethyl)-4-aminophenols et leur utilisation dans des teintures oxydantes pour cheveux Download PDF

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Publication number
WO1990003362A1
WO1990003362A1 PCT/EP1989/001063 EP8901063W WO9003362A1 WO 1990003362 A1 WO1990003362 A1 WO 1990003362A1 EP 8901063 W EP8901063 W EP 8901063W WO 9003362 A1 WO9003362 A1 WO 9003362A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
formula
aminophenols
group
developer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1989/001063
Other languages
German (de)
English (en)
Inventor
David Rose
Horst Höffkes
Edgar Lieske
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to FI911315A priority Critical patent/FI911315A0/fi
Publication of WO1990003362A1 publication Critical patent/WO1990003362A1/fr
Priority to DK91502A priority patent/DK50291D0/da
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom

Definitions

  • the invention relates to new 2- (alkoxyalkyaminomethyl) -4-aminophenols and their salts and to their use as developer components in oxidation hair colorants.
  • oxidation hair colorants play a preferred role for dyeing hair because of their intense colors and good fastness properties.
  • hair dyes contain oxidation dye precursors in a cosmetic carrier.
  • Developer substances and coupler substances are used as oxidation dye precursors.
  • the developer components form the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
  • oxidation dye precursors must first and foremost meet the following requirements: in oxidative coupling, they must form the desired color shades with sufficient intensity and authenticity. They must also have a good ability to draw up on human hair, with no noticeable differences between damaged and freshly regrown hair. They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against permanent wave fluids. Finally, they should not stain the scalp too much and, above all, they should be harmless in toxicological and dermatological terms.
  • Primary aromatic amines with a further free or substituted hydroxy or amino group located in para or ortho position, furthermore diaminopyridine derivatives, heterocyclic hydrazone derivatives and 4-aminopyrazolone derivatives are usually used as developer substances. M-Phenylenediamine derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler substances.
  • the invention relates to 2- (alkoxyalkylaminomethyl) -4-am_- nophenols of the formula (I)
  • NH in the R is hydrogen, an alkyl group with 1 to 4 carbon atoms, a hydroxyalkyl group with 2 to 4 carbon atoms, an aminoalkyl group with 2 to 4 carbon atoms which are linked to nitrogen by one or two alkyl groups with 1 to 4 carbon atoms.
  • Atoms can be substituted or their nitrogen atom a piperidine, morpholine, pyrrolidine or
  • Piperazin-Rinq belongs to or a group -C H_ -OC H_, - ° - ⁇ ⁇ m 2m n 2n + 1, and wherein m is an integer from 2-4 and n is an integer from 1-4 and their water-soluble Salts.
  • R is hydrogen.
  • the compounds of formula (1) are new. However, they can be prepared in a conventional manner by adding 2-chloromethyl-4-nitrophenol with an amine of the formula (II)
  • the new compounds of the formula (I) or their salts are suitable for use as oxidation dye precursors of the developer type in hair colorants. They are able to form dyes under the action of oxidizing agents. However, particularly intensive and brilliant dyes are formed by oxidative coupling in the presence of coupler substances.
  • oxidation dye precursors containing 2- (alkoxyalkylaminomethyl) -4-aminophenols of the formula (I) or their water-soluble salts as developer components in addition to customary developer or coupler components and, if appropriate direct hair dyes included.
  • coupler substances for the new developers of the formula (1) are, in particular, those with phenolic hydroxyl groups and those of the bis- (2,4-diaminophenyl) alkane and bis- (2,4-diami) type - Suitable nophenoxy) alkanes, as in DE-OS 32 35 615 and DE-OS 28 52 272 are described.
  • a further, particularly preferred embodiment of the invention is therefore hair dye of the abovementioned type which, as coupler component, contains phenols, naphthols, resorcinols and / or 1,3-bis- (2,4-diaminophenyl) alkanes or 1,3- Contain bis- (2,4-diaminophenoxy) alkanes.
  • Such hair dyes provide particularly intense colors in the range of red-brown to olive-brown shades.
  • the 2- (alkoxyalkylaminomethyl) -4-aminophenols of the formula (I) according to the invention can be used either as such or in the form of their water-soluble salts with inorganic or organic acids, for.
  • the developer substances and the coupler substances are generally used in equimolar amounts, but a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer substances and coupler substances in a molar ratio of 1: 0.5 to 1: 2 can be used.
  • the 2-alkoxy-alkylaminomethyl) -4-aminophenols of the formula (1) according to the invention or their salts can be used in an amount of 0.05 to 10 millimoles per 100 g of the hair dye. It is not necessary for the compounds of the formula (1) to be uniform compounds. Rather, mixtures of the compounds can also be used.
  • oxidation dye precursors e.g. B. Nitrophenylenediamine derivatives, anthraquinone dyes or indophenols can be added.
  • a suitable cosmetic carrier e.g. B. Nitrophenylenediamine derivatives, anthraquinone dyes or indophenols
  • the oxidation dye precursors and any direct dyes are incorporated into a suitable cosmetic carrier.
  • suitable cosmetic carrier are, for example, creams, emulsions, gels or also surfactant-containing, foaming solutions, for example shampoos or other preparations which are suitable for use on the hair.
  • Standard ingredients are TION such cosmetic Zube ⁇ such as wetting agents and emulsifiers such as anionic, nonionic or amphoiytician surfactants, for example fatty alcohol sulfates, alkane sulfonates, alpha-olefin sulfonates, fatty alcohol polyglycol ether sulfates, ethylene oxide adducts with fatty alcohols, fatty acids and alkylphenols, sorbitan fatty acid esters and fatty repartialglyceride, Fettklarealkanola ide as well as thickeners such as methyl or hydroxyethyl cellulose, starch, fatty alcohols, paraffin oils, fatty acids, furthermore perfume oils and hair care additives such as water-soluble cationic polymers, protein derivatives, pantothenic acid and cholesterol.
  • emulsifiers such as anionic, nonionic or amphoiytician surfactants, for example fatty alcohol sulfates, alkane sulfon
  • the components of the cosmetic carriers are used to manufacture the hair dye according to the invention! used in amounts customary for this purpose, e.g. emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
  • the oxidation dye precursors are mixed into the carrier in amounts of 0.2 to 5% by weight, preferably 1 to 3% by weight, of the total colorant.
  • a preferred form of use for the 2- (alkoxyalkylaminomethyl) -4-aminophenols of the formula (I) according to the invention are cream coloring agents in the form of an oil-in-water emulsion with an amount of
  • Alkali dithionite and ammonia in an amount to adjust the pH of the emulsion to a value between 8 and 10.
  • alkyl sulfate or alkyl ether sulfate surfactant mentioned can be present as alkali, ammonium or alkanolammonium salt with 2 or 3 carbon atoms in the alkanol group, for. B. as sodium, triethanolammonium or isopropanolammonium salt.
  • alkyl-C 1 f.-C 1 ( ether sulfate surfactant a sulfuric acid monoester salt of an adduct of 1 to 10 moles of ethylene oxide with a C. .. C. fatty alcohol can be used.
  • the oxidative development of the coloring can take place with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a lightening effect on the hair is desired.
  • Particularly suitable oxidizing agents are hydrogen peroxide or its addition products with urea, melamine or sodium borate and mixtures of such hydrogen peroxide addition products with potassium peroxodisulfate.
  • the use of the hair dye according to the invention can, regardless of the type of cosmetic preparation, for. B. as a cream, gel or shampoo, in a weakly acidic, neutral or alkaline mixture.
  • the use of the hair dye in a pH range from 8 to 10 is preferred.
  • the application temperatures can be in a range between 15 ° C. and 40 ° C. After an exposure time of approx.
  • the hair dye is removed from the hair to be colored by rinsing for 30 minutes.
  • the hair is then washed with a mild shampoo and dried. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. B. a color shampoo was used.
  • stage 1 a mixture of
  • stage 2 9.0 g (0.038 mol of substance obtained in stage 1) were catalytically reduced in ethanol.
  • stage 1 Analogously to Example 1.1, stage 1, starting from 41.3 g (0.4 mol) of 3-ethoxypropylamine and 9.4 g (0.05 mol) of 2-chloromethyl-4-nitrophenol.
  • stage 2 7.6 g (0.03 mol) of the substance obtained in stage 1 were catalytically reduced in ethanol. Yield: 6.1 g (68.5% of theory); yellow crystals, melting point: 60 73 ° C
  • stage 1 Analogously to Example 1.1, stage 1, starting from 46.99 g (0.4 mol) of 3-isopropoxypropylamine and 9.4 g (0.05 mol) of 2-chloromethyl-4-nitrophenol.
  • stage 2 Analogously to Example 1.1, stage 2, 7.3 g of substance obtained in stage 1 were catalytically reduced in ethanol. Yield: 6.7 g (80% of theory); beige crystals, melting point: 75 - 85 ° C 2. Examples of use
  • Hair colorants according to the invention were produced in the form of a hair color cream emulsion of the following composition:
  • the components were mixed together in succession. After the oxidation dye precursors and the inhibitor had been added, the pH of the emulsion was first adjusted to 9.5 with concentrated ammonia solution, and the mixture was then made up to 100 g with water.
  • the oxidative development of the color was carried out with 3% hydrogen peroxide solution as the oxidizing agent.
  • 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
  • the coloring cream was adjusted to approx. 5 cm long strands of standardized, 90% gray, but not particularly pretreated human hair applied and left there at 27 ° C. for 30 minutes. After the dyeing process had ended, the hair was rinsed, washed out with a customary shampoo and then dried.
  • the following compounds were used as couplers:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

Lesdits produits correspondent à la formule (I), où R1 représente hydrogène, un groupe alkyle avec 1 à 4 atomes de C, un groupe hydroxyalkyle avec 2 à 4 atomes de C, un groupe aminoalkyle avec 2 à 4 atomes de C, qui peut être substitué sur l'atome d'azote par un ou deux groupes alkyle avec 1 à 4 atomes de C ou dont l'atome d'azote appartient à un anneau de pipéridine, morpholine, pyrrolidine ou pipérazine ou qui est un groupe -C¿m?H2m-O-CnH2n+1, où m est un nombre entier entre 2 et 4 et n est un nombre entier entre 1 et 4. Lesdits produits et leurs sels solubles dans l'eau agissent en tant que développeurs des teintures par oxydation et servent de matières de base pour colorants d'oxydation lors de la fabrication de teintures pour cheveux. Avec les copulateurs habituels, lesdits produits donnent des teintures solides à nuances brunes à rousses.
PCT/EP1989/001063 1988-09-21 1989-09-12 2-(alkoxyalkylaminomethyl)-4-aminophenols et leur utilisation dans des teintures oxydantes pour cheveux Ceased WO1990003362A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FI911315A FI911315A0 (fi) 1988-09-21 1989-09-12 2-(alkoxialkylaminometyl)-4 -aminofenoler och anvaendning av dessa i oxidativa haorfaergaemnen.
DK91502A DK50291D0 (da) 1988-09-21 1991-03-20 2-(alkoxyalkylaminomethyl)-4-aminophenoler og anvendelse heraf i oxidationshaarfarvemidler

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3831977.2 1988-09-21
DE19883831977 DE3831977A1 (de) 1988-09-21 1988-09-21 2-(alkoxyalkylaminomethyl)-4-aminophenole und deren verwendung in oxidationshaarfaerbemitteln

Publications (1)

Publication Number Publication Date
WO1990003362A1 true WO1990003362A1 (fr) 1990-04-05

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ID=6363361

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1989/001063 Ceased WO1990003362A1 (fr) 1988-09-21 1989-09-12 2-(alkoxyalkylaminomethyl)-4-aminophenols et leur utilisation dans des teintures oxydantes pour cheveux

Country Status (4)

Country Link
EP (2) EP0435884A1 (fr)
DE (1) DE3831977A1 (fr)
DK (1) DK50291D0 (fr)
WO (1) WO1990003362A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ233654A (en) * 1989-05-18 1993-02-25 Bristol Myers Squibb Co 2-aminomethyl-5-aminophenol derivatives; hair dye compositions containing them
GB2341579B (en) 1998-09-16 2003-04-16 Agra Vadeko Inc Apparatus and method of marking polymer-based laminates

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0226072A1 (fr) * 1985-12-07 1987-06-24 Wella Aktiengesellschaft Colorant d'oxydation à base de 4-amino-2-aminométhyl-phénol

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0226072A1 (fr) * 1985-12-07 1987-06-24 Wella Aktiengesellschaft Colorant d'oxydation à base de 4-amino-2-aminométhyl-phénol

Also Published As

Publication number Publication date
DK50291A (da) 1991-03-20
EP0435884A1 (fr) 1991-07-10
DK50291D0 (da) 1991-03-20
EP0364731A1 (fr) 1990-04-25
DE3831977A1 (de) 1990-04-05

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